How to prevent emails from a specific address going to Hotmail SPAM? - spam

I have a site on a dedicated server with it's own IP range that has been running for a good few years. We have a notification email address (mailout#domain.com) which we use to send automated emails (activation emails when a user signs up and notification emails if something relevant to them happens, eg someone befriends them or comments on their picture etc). Users can select whether to receive these notifications or not. We have SPF and RDNS setup.
Email from all our other email accounts go to hotmail/gmail/yahoo mail etc correctly into the inbox. However any mail sent from the mailout#domain.com account (whether automatically by the server or manually via outlook) is delivered correctly to the inboxes for yahoo and gmail however goes into Junk in Hotmail (but other #domain.com addresses deliver to hotmail's inbox correctly). It says at the top of the message that MS Smartscreen marked this message as junk. I signed up for MS Smart Network Data Services to monitor the IP and it says it's not blocked but it displays Bot-like behaviour (which kind of makes sense as our notifications are kind of bot like even though they're not spam).
I can't work out what to do to prevent this from happening, we've authenticated the email, there's obviously not a general block on the IP as emails from different accounts on the same domain are going through successfully. It doesn't seem to be the format of the email either because if I send identical emails from mailout#domain.com and contact#domain then the one from contact# gets through to the inbox but the one from mailout# goes through to junk.
I can't really work out what to do and obviously trying to get MS to sort it out is never going to happen and i've used all their available tools. I can obviously try setting up a new email address (eg noreply#domain.com) and using that for notifications but i assume it will only be a matter of time before that gets blocked as well.
I would be immensely grateful for any suggestions anyone has!
Thanks so much,
Dave

You don't have many options. Try to do as many of the following as you can:
Reach out to MS support (don't discard this notion)
Implement DKIM and possibly DMARC (which are vastly more informative than SPF)
Change your IP address to something cleaner
Find and follow bulk sender best practices, e.g. M³AAWG's BCPs, perhaps the Help – I'm on a Blocklist doc

Related

Email phishing detection issue on GoDaddy / mailgun can it be connected with DMARC?

Some email clients consider our emails as a phishing (in Office 365). The only thing that was missing based on the https://mxtoolbox.com/SuperTool.aspx?action=mx was DMARC entry missing.
I've added TXT DNS record like this (TTL 1hr):
v=DMARC1;p=none;pct=100;rua=mailto:postmaster#mydomain.com
Can it resolve the issue? Is there any specific action required to make it work with Mailgun / GoDaddy?
Thanks in advance for any help/info.
Since you have p=none, it won't resolve the issue, you need to inform the mail server to reject the email. Basically, you're just in monitoring mode with p=none.
What that being said, it sounds like you're saying Office 365 is regarding your emails as a phishing attempt. I think you might be hitting their spam filter based on certain keywords. Send an email to yourself and look at the PCL in the email headers in the outlook account and see what it says.
If you don't know how to see view the headers and just want to make it easy, you can use an inbox tester that will show you the headers.
You can also open a ticket with Microsoft and ask them why the PCL is high on your emails. They might be able to assist.
Link to: Microsoft Sender Support
Another good thing to do is to go through this Email Checker Guide, it touches on every aspect of sending email. You might have a mis-configuration someplace that's causing the issue.

Seeing a lot of SendGrid Activity marked "Deferred" after disabling a mailbox

Using SendGrid through Azure (free version).
I recently disabled a user's email because it was receiving way too much SPAM. Prior to doing this my activities list was about 1-2 pages long with recognizable e-mails my system was sending out per customer input in a website (there is a workflow for forms which the user inputs, then my system sends out an e-mail confirming input).
Now that I have disabled that e-mail, I am seeing upwards of 59 pages of activity just for one day (since I disabled the e-mail address), most of which is listed as "Deferred" or "Processed". The lists include SPAM e-mail addresses (something-reverse-mortgage#whatever.net, etc.).
Reading the SendGrid documentation, it seems that "Deferred" activities just mean that the receiving ISP is asking SendGrid to slow down. I take this to mean that my server is sending these e-mails.
This is worrisome obviously. Disabling that e-mail has this unintended consequence of seeing hundreds of "Defered" activity listings in SendGrid.
I am confused, however, if this is just the system getting these e-mails and then trying to bounce them back through my server. Since it's SPAM and likely not a real e-mail address, is SendGrid just trying to return the e-mails? Hence the activity?
If so, is this something that will eventually die down, or should I do something to prevent SendGrid from returning these obviously bogus SPAM e-mails to what it thinks is the originating sender?
Thanks in advance.
I send about 100K emails a month with sendgrid and I don't worry at all about deferred. About 1/3 of my outgoing emails are gmail and gmail is very agressive at blocking emails when you send more than 50 or so at once. They simply reject and sendgrid tries again later. They all seem to go thru within about 24 hours.

SMTP Client - Send hidden information that can come back in a reply

I am using the nodemailer SMTP node module, a simple way to send emails through SMTP.
I am using this to send out text messages to various cell carriers, which will allow you to send a text message for free via email. An example email, which will text the Sprint phone (310) 987-6543:
3109876543#messaging.sprintpcs.com
These are all going out through one SMTP email address. This means all text replies from someone's phone will channel back to my email address.
A lot of people send these texts. I want to route the reply text back to the right person, using my own server side code.
The problem is distinguishing where the text came from. Ideally I could hide my own primary key ID for the sender in some sort of SMTP header, which would arrive at the recipients phone and come straight back in their text reply.
I don't really know anything about SMTP or email protocols - is this possible?
edit
As given in each of the answers below, in better email servers you can address to an email address as well as an extension to that address, such as:
// original email
sms-service#mysite.com
// extension
sms-service+a6e1087b#mysite.com
This would be a correct answer and would solve my problem, if only this worked in Exchange Server, which is the email server I am using. I don't know if there is a way to enable this or any other workaround.
Exchange server doesn't support plus addressing natively but it is possible do achieve this with a custom MTA, e.g. http://durdle.com/regexcatchall/
Source: https://serverfault.com/questions/195276/does-exchange-support-plussed-users-e-g-mynamespamexample-com-or-a-similar
Here are a few approaches that you might be able to use:
Unique from addresses
You could you use unique "from" or "reply-to" address for each each message (or for each recipient). For example "sms-service+a6e1087b#mysite.com". In that example, the hex would be a unique identifier that can be mapped to the conversation in your database.
Gmail supports such a scheme: emails targeted to [foo]+[whatever]#gmail.com will be delivered to [foo]#gmail.com and the receiver will know also get the [whatever] back. (more on this http://lifehacker.com/144397/instant-disposable-gmail-addresses)
Identify the user, not the conversation
One option is to not identify the conversation, but identify the phone number the reply comes back from instead. In many cases, the number from where the SMS reply was sent back from is enough to connect that message to the conversation. I'm sure the SMS gateway you're using will provide you with the number from where the reply came from.
Commercial SMS gateway
You can also opt to use a commercial SMS gateway (smsglobal.com comes to mind, though there are many others). These services have well defined APIs for sending a receiving replies. This naturally comes at a price, though. But along with the price, you do get more confidence as to the reliability of the service. A free SMS gateway might get shut down without much warning.
This common problem is traditionally implemented using the semantics of From: and Reply-To: headers of e-mails. This is in fact not (directly) related to SMTP, but rather to ARPA network text messages.
RFC 5322 is the current specification of these messages. It states:
When the "Reply-To:" field is present, it indicates the address(es) to which the author of the message suggests that replies be sent. In the absence of the "Reply-To:" field, replies SHOULD by default be sent to the mailbox(es) specified in the "From:" field unless otherwise specified by the person composing the reply.
So you simply need to encode the information you need into the Reply-To: header. Since you mention your own server-side code, you might be running an SMTP server yourself. In this case, you can put any address that will be routed to your SMTP server and encode the right person's address there.
Alternatively, if you rely on another SMTP server, you might want to use aliases. Postfix, and mail services such as GMail, typically allow address extensions, i.e. addresses of the form user+foo#domain.com, and you can encode the necessary information in the address extension.
For example, let's say that alice#domain.com wants to send a text to Sprint phone (310) 987-6543 through your service, you could send an e-mail to 3109876543#messaging.sprintpcs.com with:
Reply-To: alice%40domain.com#yourservice.com
Alternatively:
Reply-To: yourservice+alice%40domain.com#gmail.com
This will allow you to route the reply properly by looking at the destination of the reply e-mail.

Unable to send to unresolved email addresses although configured in settings

I want to send an email in a workflow from a hard coded email address and I have made sure that the option is set to allow this in system settings but I still cant get it work.
Have I missed another setting? Or does this option only allow unresolved emails in the "To" field?
I shouldnt have thought that would work from a hardcoded email address.
Crm doesnt send emails itself, it either uses the users outlook, or uses email router - both of which requrie a system user record.
In the case of the outlook it is really sent by the user, in the case of the email router it is generally sent from exchange.
Crm cant just pretend to be an email address.
The CRM usually takes 10-12 hours to send email to un-resolved email addresses after the setting has been turned on.
Maybe waiting helps

Monotouch: any ideas why sending mail is sporadic?

This is the code: d59516457">http://monobin.com/_d59516457
These are the results when using Debug|iPhone (Debug|Simulator works fine):
When the "From" is set to GMail, I can only send to a GMail account.
When the "From" is set to my ISP, I can send to myself (at the ISP) and GMail, but NOT to another of my email addresses not connected to the ISP. (it's to an address for one of my websites, which is then forwarded to my ISP).
Any ideas why this is so flakey? I thought at first it was the ISP, but now I'm not so sure.. is there a way to "trace" any of hops?
I'm concerned that if I submit it to the app store, a user will have the same problem as this, and I don't want a bad rep for the app. On the other hand, because it works, sometime and not others, maybe I could hope it's my phone?
if you want you can use http://testflightapp.com/ so you get some beta testers doing Ad-Hoc releases of your app (you choose who you want to invite), if you want so I can send you an invite I would be more than glad to help you to test your app :) email me if you want the invite, my email its on my profile
About the solution, you can check if you have a webmail based interface that you can view on your computer, the email that you sent from the iPhone must be on the sent items folder, if the email and the attachment are there you can be sure that your application is delivering correctly you email to the SMTP server so the problem resides somewhere else...
Also make sure your that your smtp server is not blacklisted as a SPAM server even more if your smtp server relies on shared enviroment like Hostgator shared plans etc
Alex

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